2-Bromo-4-nitro-1-[(propan-2-yl)oxy]benzene → 3-Bromo-4-(1-methylethoxy)benzenamine

Participants

Reaction Steps

Platinum oxide (50 mg) was added to a solution of 2-isopropoxy-5-nitrobromobenzene (1.7 g, 6.5 mmol) in ethyl acetate (50 ml) and the mixture was stirred under hydrogen (50 psi) for 1 hour. The mixture was filtered, further platinum oxide (50 mg) was added and the mixture was stirred under hydrogen (50 psi) for 1 hour. The mixture was filtered and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography, eluting with hexane/EtOAc (80:20), to give the title compound (0.92 g, 62%); δH (360MHz, CDCl3) 1.32 (3H, d, J 5.6Hz, OCH(CH3)2), 4.33 (1H, m, OCH(CH3)2), 6.57 (1H, dd, J 8.7, 2.8Hz, 6-H), 6.78 (1H, d, J 8.7Hz, 5-H), 6.91 (1H, d, J 2.8 Hz, 2-H).

Provenance & Evidence